4-Iodo-N,N-diphenylaniline

Name: 4-Iodo-N,N-diphenylaniline
Brand: ChemScene
Availability: InStock
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CAS No. 38257-52-2
Cat. No. CS-0040974
Molecule weight371.21
Purity≥98%
MDL No.MFCD11046352

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Structure of 38257-52-2

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General Information

CAS No. 38257-52-2
Cat. No. CS-0040974
Purity ≥98%
MDL No. MFCD11046352
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₁₄IN
Molecular Weight 371.21
Synonym(s) (4-Iodo-phenyl)-diphenyl-amine
SMILES IC1=CC=C(N(C2=CC=CC=C2)C3=CC=CC=C3)C=C1

Description

4-Iodo-N,N-diphenylaniline features a para-iodinated aniline core with two bulky diphenylamino substituents, conferring enhanced steric protection and stability. This electron-rich scaffold enables efficient coupling in palladium-catalyzed cross-coupling reactions, particularly in the synthesis of functionalized biaryls and advanced organic semiconductors.

Application

4-Iodo-N,N-diphenylaniline serves as a versatile building block in palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl architectures. The iodide moiety provides high reactivity in Suzuki, Stille, and Negishi couplings, while the N,N-diphenylamino group imparts excellent bench stability and facilitates purification. Its defined steric and electronic profile supports predictable regiochemistry in complex molecule synthesis.

Synthesis

Route1
- In-stock
  
  624-38-4
- 122-39-4
- ~92%
- In-stock
  
  38257-52-2
References
- Amro, Kassem; Daniel, Jonathan; Clermont, Guillaume; Bsaibess, Talia; Pucheault, Mathieu; Genin, Emilie; Vaultier, Michel; Blanchard-Desce, Mireille Tetrahedron, 2014 , vol. 70, # 10 p. 1903 - 1909
Route2
- In-stock
  
  624-38-4
- In-stock
  
  90-30-2
- ~42%
- In-stock
  
  38257-52-2
References
- Paine, Anthony James Journal of the American Chemical Society, 1987 , vol. 109, # 5 p. 1496 - 1502
Route3
- In-stock
  
  36809-26-4
- ~92%
- In-stock
  
  38257-52-2
References
- Fang, Jing-Kun; An, De-Lie; Wakamatsu, Kan; Ishikawa, Takeharu; Iwanaga, Tetsuo; Toyota, Shinji; Matsuo, Daisuke; Orita, Akihiro; Otera, Junzo Tetrahedron Letters, 2010 , vol. 51, # 6 p. 917 - 920

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 3.24
LogP 5.761
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Composite Block Small Molecule Semiconductor Synthesis Building Block

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Tertiary Arylamines

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4-Iodo-N,N-diphenylaniline

CAS No. 38257-52-2

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